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$64+ Cheap flights from Chesapeake, VA to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Chesapeake to Massachusetts

Keep the following information in mind while searching for Chesapeake to Massachusetts flight deals. Data was last updated July 31, 2025.

Round-trip from

$103
(Breeze Airways)

One-way from

$64
(Breeze Airways)

Popular in

December

Cheapest in

August

Average price

$167
From Chesapeake to Massachusetts
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One-way flight from Chesapeake to Massachusetts
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Highest demand for flights based on searches. 28% potential increase in price ($101 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chesapeake to Massachusetts

Cheapest flights from Chesapeake to Massachusetts
Explore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Gotogate deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/410:20 amORF - BOS
Nonstop1h 36mAllegiant Air
Mon 8/1112:46 pmBOS - ORF
Nonstop1h 39mAllegiant Air
Deal found 7/31$95
This Breeze Airways deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:32 amORF - BDL
Nonstop1h 27mBreeze Airways
Sun 9/218:15 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 7/30$103
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1110:20 amORF - BOS
Nonstop1h 36mMultiple Airlines
Fri 8/156:30 amBOS - ORF
1 stop6h 14mMultiple Airlines
Deal found 7/31$143
This JetBlue deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/265:57 pmORF - BOS
Nonstop1h 40mJetBlue
Tue 9/23:18 pmBOS - ORF
Nonstop1h 44mJetBlue
Deal found 7/29$147
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1311:53 amORF - BOS
Nonstop1h 52mDelta
Tue 8/199:20 amBOS - ORF
Nonstop1h 52mDelta
Deal found 7/29$172
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:39 pmORF - BOS
1 stop8h 55mSpirit Airlines
Tue 8/1910:34 amBOS - ORF
1 stop5h 51mSpirit Airlines
Deal found 7/29$175
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2312:50 pmORF - BOS
1 stop6h 09mAmerican Airlines
Fri 9/2610:30 amBOS - ORF
1 stop6h 34mAmerican Airlines
Deal found 7/29$177
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/911:30 amORF - BDL
1 stop5h 50mAmerican Airlines
Sat 9/136:00 amBDL - ORF
1 stop3h 26mAmerican Airlines
Deal found 7/29$196
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2711:43 amORF - ALB
1 stop6h 14mDelta
Wed 9/32:25 pmALB - ORF
1 stop6h 47mDelta
Deal found 7/30$197
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2110:02 pmORF - BOS
1 stop10h 33mFrontier
Sun 8/249:20 amBOS - ORF
1 stop11h 47mFrontier
Deal found 7/30$198
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:30 amORF - BDL
2 stops8h 40mSouthwest
Sat 10/45:30 amBDL - ORF
1 stop3h 50mSouthwest
Deal found 7/30$202
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1311:45 amORF - BOS
1 stop5h 20mSouthwest
Wed 8/205:20 amBOS - ORF
2 stops9h 40mSouthwest
Deal found 7/29$207

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Chesapeake to Massachusetts that are best for you.

Fly from

Chesapeake

Fly to

Massachusetts

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 9/18

10:32 am-11:59 am

Nonstop1h 27m

Hartford Bradley Intl

Sun 9/21

8:15 am-9:52 am

Nonstop1h 37m

$103

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Mon 8/11

10:20 am-11:56 am

Nonstop1h 36m

Boston Logan Intl

Fri 8/15

6:30 am-12:44 pm

1 stop6h 14m

$143

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Tue 8/26

5:57 pm-7:37 pm

Nonstop1h 40m

Boston Logan Intl

Tue 9/2

3:18 pm-5:02 pm

Nonstop1h 44m

$147

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Wed 8/13

11:53 am-1:45 pm

Nonstop1h 52m

Boston Logan Intl

Tue 8/19

9:20 am-11:12 am

Nonstop1h 52m

$172

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Mon 8/18

1:39 pm-10:34 pm

1 stop8h 55m

Boston Logan Intl

Tue 8/19

10:34 am-4:25 pm

1 stop5h 51m

$175

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Tue 9/23

12:50 pm-6:59 pm

1 stop6h 09m

Boston Logan Intl

Fri 9/26

10:30 am-5:04 pm

1 stop6h 34m

$177

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Tue 9/9

11:30 am-5:20 pm

1 stop5h 50m

Hartford Bradley Intl

Sat 9/13

6:00 am-9:26 am

1 stop3h 26m

$196

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 9/18

6:15 am-9:36 am

1 stop3h 21m

Hartford Bradley Intl

Sun 9/21

6:00 am-9:24 am

1 stop3h 24m

$197

NorfolkAlbany

ORF - ALB

ORFALB

Norfolk

Wed 8/27

11:43 am-5:57 pm

1 stop6h 14m

Albany Intl

Wed 9/3

2:25 pm-9:12 pm

1 stop6h 47m

$197

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 8/21

10:02 pm-8:35 am

1 stop10h 33m

Boston Logan Intl

Sun 8/24

9:20 am-9:07 pm

1 stop11h 47m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 45 results
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Best time to book a flight from Chesapeake to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chesapeake with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Massachusetts

What is the cheapest month to book a flight from Chesapeake to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $218). Flying from Chesapeake to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from C6E to MA?

Find hourly flight availability from Chesapeake to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Chesapeake to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chesapeake to Massachusetts

Explore weekly flight availability from Chesapeake to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 31, 2025.

The most flights from C6E to USMA are scheduled on a Thursday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Breeze Airways from Chesapeake to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Chesapeake to Massachusetts flight route?

    Within the past month, 13 users have taken a look at flights from Chesapeake to Massachusetts.

  • What are the cheapest airlines to fly from Chesapeake to Massachusetts one-way?

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $64. Users have also found prices from $82 and $84 on Spirit Airlines and JetBlue, respectively.

  • What are the most popular routes from Chesapeake to Massachusetts?

    When deciding which route to take from Chesapeake to Massachusetts consider Norfolk - Boston Logan Intl, Norfolk - Albany Intl or Norfolk - Hartford Bradley Intl as they are the most popular.

  • What are the most reliable airlines from Chesapeake to Massachusetts?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chesapeake to Massachusetts on time: Aeromexico (99%), Korean Air (98%), WestJet (96%).

  • What are the cheapest flights from Chesapeake to Massachusetts?

    The cheapest flight price from Chesapeake to Massachusetts is $83. On average you can expect to pay $3,274. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $118.

  • Can I find deals for flights from Chesapeake to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Massachusetts.

  • Can I find deals for business class flights from Chesapeake to Massachusetts?

    Yes. Cheapflights offers flight deals from Chesapeake to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $218). Flying from Chesapeake to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 7 airlines flying from Chesapeake to Massachusetts

Discover the top 7 airlines that operate flights from Chesapeake to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$48Average$90FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$64Average$156FlexibilityNo cancel feeOn-time65%
DeltaCheapest$94Average$284FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$97Average$233FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$166Average$334FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$168Average$370FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$171Average$338FlexibilityNo cancel feeOn-time71%

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